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In a three-necked flask fitted with a condenser, a suspension of copper II chloride (370 mg, 2.75 mmol) in acetonitrile (5 mL) was treated with tert-butyl nitrite (0.41 mL, 3.44 mmol) and stirred at rt for 10 minutes. A solution of 2-amino-6-trifluoromethylbenzthiazole (500 mg, 2.29 mmol) in acetonitrile (1 mL) was then added dropwise. The mixture was heated at 65° C. for 30 minutes, then cooled and diluted with an excess of 1 N aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate. The organic phase was separated, dried (MgSO4), and concentrated under reduced pressure. An orange semi-solid (501 mg, 92percent) was obtained and used without further purification. 1H NMR (300 MHz, CDCl3) delta 8.10-8.05 (m, 2H), 7.74 (d, 1H); LC-MS m/z 238.2 (MH+), ret. time 3.76 min TLC Rf=0.50 (9:1 hexanes/ethyl acetate).
With hydrogenchloride; tert.-butylnitrite; copper dichloride; In acetonitrile; at 20℃;
8.25 ml tert-butyl nitrite were added to a solution of 7.40 g copper (II) chloride in 120 ml acetonitrile. The reaction mixture was stirred ten minutes at room temperature. Then a solution of 10.0 g 2-Amino-6-(trifluoromethyl)benzonitrile were added. Then 100 ml 1 N HCI were added to the cooled reaction mixture. The reaction mixture was extracted five times with portions of 50 ml ethyl acetate. The combined organic layers were washed with water and the dried over MgSO4. The solvent was removed in vacuo to obtain 9.79 g crude 2-Chloro-6-trifluoromethyl-benzothiazole as a red oil which solidifies upon standing. This material was used without further purification. C8H3CIF3NS (237.63), MS(GC): 237.0 (M+H+), Rf(n-heptane :ethyl acetate = 1 :1) = 0.72 .
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